2-Decarboxy-2-aminomethyl-6-keto-PG compounds

ABSTRACT

The present invention relates to novel 2-decarboxy-2-aminomethyl-6-keto-PG compounds, which are useful for inducing a variety of prostacyclin-like pharmacological effects. Accordingly, these compounds are useful pharmacological agents for the same purposes for which prostacyclin is employed.

CROSS REFERENCE TO RELATED APPLICATION

The present application is a divisional application of copendingapplication Ser. No. 959,400, filed Nov. 9, 1978; which is a divisionalapplication of Ser. No. 819,857, filed July 28, 1977, now U.S. Pat.4,158,667; which is a continuation-in-part of Ser. No. 725,548, filedSept. 22, 1976, now abandoned; which is a continuation-in-part of Ser.No. 716,972, filed Aug. 23, 1976, now abandoned; which is acontinuation-in-part of Ser. No. 655,110, filed Feb. 4, 1976, nowabandoned.

BACKGROUND OF THE INVENTION

The present invention relates to novel2-decarboxy-2-aminomethyl-6-keto-PG compounds, which are useful forinducing a variety of prostacyclin-like pharmacological effects.Accordingly, these compounds are useful pharmacological agents for thesame purposes for which prostacyclin is employed.

The essential material constituting a disclosure of the preparation anduse of the novel compounds of the present invention are incorporatedhere by reference from U. S. Pat. No. 4,158,667.

SUMMARY OF THE INVENTION

The present invention particularly provides:

A compound of the formula ##STR1## wherein W₁ is α-OH:β-H, α-H:β-OH,oxo, methylene, α-H:β-H, α-CH₂ OH:β-H;

wherein L is

(1) --(CH₂)_(d) --C(R₂)₂,

(2) --CH₂ --O--CH₂ --Y--, or

(3) --CH₂ CH═CH--,

wherein d is zero to 5, R₂ is hydrogen, methyl, or fluoro, being thesame or different with the proviso that one R₂ is not methyl when theother is fluoro, and wherein Y is a valence bond, --CH₂ -- or --(CH₂)₂,

wherein Q is keto, α-H:β:H, α-OH:β-R₈ or α-R₈ :β-OH

wherein R₈ is hydrogen or alkyl of one to 4 carbon atoms, inclusive;

wherein R₉ is hydrogen, methyl, or ethyl, and R₁₈ is hydrogen, alkyl ofone to 4 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms,inclusive, phenyl, or phenyl substituted with alkyl of one to 4 carbonatoms, inclusive;

wherein R₅ and R₆ are hydrogen, alkyl of one to 4 carbon atoms,inclusive, or fluoro, being the same or different, with the proviso thatone of R₅ and R₆ is fluoro only when the other is hydrogen or fluoro andthe further proviso that neither R₅ nor R₆ is fluoro when

Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C_(j)H_(2j), wherein C_(j) H_(2j) is a valence bond or alkylene of one to 9carbon atoms, inclusive, with one to 6 carbon atoms, inclusive betweenCR₅ R₆ -- and the phenyl ring;

wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro,trifluoromethyl, or --OR₇ --, wherin R₇ is alkyl of one to 4 carbonatoms, inclusive, and s is zero, one, 2, or 3, with the proviso that notmore than two T's are other than alkyl and when s is 2 or 3 the T's areeither the same or different; and

wherein X is

(1) trans--CH═CH--,

(2) cis--CH═CH--,

(3) --CC--, or

(4) --CH₂ CH₂ --;

including the lower alkanoates thereof.

With regard to the divalent substituents described in the claims, e.g.,Q and W₁, these divalent radicals are defined as α-R_(i) :β-R_(j), whereR_(i) represents a substituent of the divalent moiety of the alphaconfiguration with respect to the cyclopentane and R_(j) represents asubstituent of the divalent moiety of the beta configuration withrespect to the cyclopentane ring. Accordingly, when Q is defined asα-OH:β-R₈, the hydroxy of the Q moiety is in the alpha configuration,i.e., as in prostacyclin, and the R₈ substituent is in the betaconfiguration. Not all carbon atoms to which such divalent moieties areattached represent asymmetric centers. For example, when both valencebonds are to hydrogen (e.g., W₁ or Q is α-H:β-H), then no asymmetriccenter is present.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The present invention particularly relates to the following chemicalcompounds:

2-Decarboxy-2-aminomethyl-6-keto-11β-16-phenoxy-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-11-deoxy-16-phenoxy-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-13,14-didehydro-15(S)-16-phenoxy-17,18,19,20-tetranor-PGF₁;

2-Decarboxy-2-aminomethyl-6-keto-13,14-didehydro-(15R)-16-phenoxy-17,18,19,20-tetranor-PGF₁;

2-Decarboxy-2-aminomethyl-6-keto-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6,15-diketo-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-phenoxy-17,18,19,20-tetranor-PGF₁.alpha.;

2-Decarboxy-2-aminomethyl-6-keto-16-phenoxy-17,18,19,20-tetranor-PGF₁.alpha.,11,15-diacetate;

2-Decarboxy-2-aminomethyl-6,15-diketo-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1α;

2-Decarboxy-2-aminomethyl-6-keto-17-phenyl-18,19,20-tetranor-PGF₁.alpha.;

2-Decarboxy-2-aminomethyl-6-keto-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-phenyl-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-PGF.sub.1α;

2-Decarboxy-2-aminomethyl-6-keto-17-(p-fluorophenyl)-18,19,20-trinor-PGF.sub.1α;

2-Decarboxy-2-aminomethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trianor-PGF.sub.1α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-methyl-16-phenoxy-18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16,16-phenoxy-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16,16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-PGF₁.alpha.;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl)-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-tetranor-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-13,14-diehydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α;

2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF₁α; and

2-Decarboxy-2-aminomethyl-6-keto-17-phenyl-18,19,20-trinor-PGF₁α.

I claim:
 1. A prostacyclin intermediate of formula ##STR2## wherein W₁is α--OH:β--H:β--OH, oxo, methylene, α--H:β--H, α--CH₂ OH:β--H;wherein Lis(1) --(CH₂)_(d) --C(R₂)₂ --, (2) --CH_(2--O--CH) ₂ --Y--, or (3) --CH₂CH═CH--, wherein d is zero to 5, R₂ is hydrogen, methyl, or fluoro,being the same or different with the proviso that one R₂ is not methylwhen the other is fluoro, and wherein Y is a valence bond, --Ch₂ -- or--(CH₂)₂ --, wherein Q is keto, α--H:β--H, α--OH:β--R₈ or α--R₈ :β--OHwherein R₈ is hydrogen or alkyl of one to 4 carbon atoms, inclusive;wherein R_(g) is hydrogen, methyl, or ethyl, and R₁₈ is hydrogen, alkylof one to 4 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms,inclusive, phenyl, or phenyl substituted with alkyl of one to 4 carbonatoms, inclusive; wherein R₅ and R₆ are hydrogen, alkyl of one to 4carbon atoms, inclusive, or fluoro, being the same or different, withthe proviso that one of R₅ and R₆ is fluoro only when the other ishydrogen or fluoro and the further proviso that neither R₅ nor R₆ isfluoro when Z is oxa (--0--); wherein Z represents an oxa atom (--0--)or C_(j) H_(2j), wherein C_(j) H_(2j) is a valence bond or alkylene ofone to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusivebetween CR₅ R₆ -- and the phenyl ring; wherein T is alkyl of one to 4carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR₇ --,wherein R₇ is alkyl of one to 4 carbon atoms, inclusive, and s is zero,one, 2, or 3, with the proviso that not more than two T's are other thanalkyl and when s is 2 or 3 the T's are either the same or different; andwherein X is(1) trans--CH═CH--, (2) cis--CH═CH--, (3) --C↑C--, or (4)--CH₂ CH₂ --; including the lower alkanoates thereof.
 2. A compoundaccording to claim 1, wherein W₁ is α-H:β-OH. 3.2-Decarboxy-2-aminomethyl-6-keto-11β-16-phenoxy-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 2. 4. A compound according to claim 1,wherein W₁ is oxo.
 5. A compound according to claim 1, wherein W₁ ismethylene.
 6. A compound according to claim 1, wherein W₁ is α-H:β-H. 7.2-Decarboxy-2-aminomethyl-6-keto-11-deoxy-16-phenoxy-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 6. 8. A compound according to claim 1,wherein W₁ is α-CH₂ OH:β-H.
 9. A compound according to claim 1, whereinW₁ is α-OH:β-H, wherein L is --(CH₂)_(n), n being 3, 4, or 5, andwherein Q is oxo or α-OH:-β-R₈.
 10. A compound according to claim 9,wherein X is --C.tbd.C--. 11.2-Decarboxy-2-aminomethyl-6-keto-13,14-didehydro-15(S)-16-phenoxy-17,18,19,20-tetranor-PGF₁,a compound according to claim
 10. 12.2-Decarboxy-2-aminomethyl-6-keto-13,14-dihydro-(15R)-16-phenoxy-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 10. 13. A compound according to claim 9,wherein X is --CH₂ CH₂ --. 14.2-Decarboxy-2-aminomethyl-6-keto-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 13. 15.2-Decarboxy-2-aminomethyl-6,15-diketo-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 13. 16. A compound according to claim 9,wherein X is trans--CH═CH--. 17.2-Decarboxy-2-aminomethyl-6-keto-16-phenoxy-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 16. 18.2-Decarboxy-2-aminomethyl-6-keto-16-phenoxy-17,18,19,20-tetranor-PGF₁α,11,15-diacetate, a compound according to claim
 16. 19.2-Decarboxy-2-aminomethyl-6,15-diketo-16-phenoxy-17,18,19,20-tetranor-PGF₁.alpha.,a compound according to claim
 16. 20.2-Decarboxy-2-aminomethyl-6-keto-17-phenyl-18,19,20-trinor-PGF₁α, acompound according to claim 16.21.2-Decarboxy-2-aminomethyl-6-keto-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 13. 22.2-Decarboxy-2-aminomethyl-6-keto-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 10. 23.2-Decarboxy-2-aminomethyl-6-keto-17-phenyl-18,19,20-trinor-cis-13-PGF₁.alpha.,a compound according to claim
 9. 24.2-Decarboxy-2-aminomethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 25.2-Decarboxy-2-aminomethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 26.2-Decarboxy-2-aminomethyl-6-keto-17-(p-fluorophenyl)-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 27.2-Decarboxy-2-aminomethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 28.2-Decarboxy-2-aminomethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 29.2-Decarboxy-2-aminomethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 1. 30.2-Decarboxy-2-aminomethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 1. 31.2-Decarboxy-2-aminomethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 1. 32.2-Decarboxy-2-aminomethyl-6-keto-16-methyl-16-phenoxy)-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 33.2-Decarboxy-2-aminomethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 34.2-Decarboxy-2-aminomethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 35.2-Decarboxy-2-aminomethyl-6-keto-17-(m-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1α,a compound according to claim
 1. 36.2-Decarboxy-2-aminomethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 37.2-Decarboxy-2-aminomethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁.alpha.,a compound according to claim
 1. 38.2-Decarboxy-2-aminomethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 39.2-Decarboxy-2-aminomethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 40.2-Decarboxy-2-aminomethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 41.2-Decarboxy-2-aminomethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGF₁.alpha.,a compound according to claim
 1. 42.2-Decarboxy-2-aminomethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 43.2-Decarboxy-2-aminomethyl-6-keto-17-(m-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 44.2-Decarboxy-2-aminomethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁.alpha.,a compound according to claim
 1. 45.2-Decarboxy-2-aminomethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 46.2-Decarboxy-2-aminomethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1α,a compound according to claim
 1. 47.2-Decarboxy-2-aminomethyl-6-keto-16-(m-chlorophenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 48.2-Decarboxy-2-aminomethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1α,a compound according to claim
 1. 49.2-Decarboxy-2-aminomethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 50.2-Decarboxy-2-aminomethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF.sub.1α,a compound according to claim
 1. 51.2-Decarboxy-2-aminomethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 52.2-Decarboxy-2-aminomethyl-6-keto-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 53.2-Decarboxy-2-aminomethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 54.2-Decarboxy-2-aminomethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 55.2-Decarboxy-2-aminomethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF₁.alpha.,a compound according to claim
 1. 56.2-Decarboxy-2-aminomethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α,a compound according to claim
 1. 57.2-Decarboxy-2-aminomethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF₁.alpha.,a compound according to claim
 1. 58.2-Decarboxy-2-aminomethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 59.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 60.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF₁.alpha.,a compound according to claim
 1. 61.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 62.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-PGF₁.alpha.,a compound according to claim
 1. 63.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 64.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro,16,16-difluoro-17-phenyl-18,19,20-trinor-PGF₁.alpha.,a compound according to claim
 1. 65.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 1. 66.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 1. 67.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 1. 68.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1α,a compound according to claim
 1. 69.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 70.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1α,a compound according to claim
 1. 71.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 72.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁.alpha.,a compound according to claim
 1. 73.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 74.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 75.2-Decarboxy-2-aminomethyl-6-keto-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁.alpha.,a compound according to claim
 1. 76.2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF₁.alpha.,a compound according to claim
 1. 77.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 78.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 79.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 80.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 81.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 82.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 83.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 84.2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 85.2-Decarboxy-2-aminomethyl-6-keto-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1α,a compound according to claim
 1. 86.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 87.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 88.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 89.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 90.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 91.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF₁.alpha.,a compound according to claim
 1. 92.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 93.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 94.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF₁.alpha.,a compound according to claim
 1. 95.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF₁.alpha.,a compound according to claim
 1. 96.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF₁α,a compound according to claim
 1. 97.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α,a compound according to claim
 1. 98.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α,a compound according to claim
 1. 99.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α,a compound according to claim
 1. 100.2-Decarboxy-2-aminomethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 101.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 102.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 103.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 104.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 105.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 106.2-Decarboxy-2-aminomethyl-6-keto-3-oxa16,16-difluoro-17-phenyl-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 107.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 1. 108.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 1. 109.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF₁α,a compound according to claim
 1. 110.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF₁.alpha.,a compound according to claim
 1. 111.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-PGF₁α,a compound according to claim
 1. 112.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁.alpha.,a compound according to claim
 1. 113.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 114.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 115.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF₁.alpha.,a compound according to claim
 1. 116.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁.alpha.,a compound according to claim
 1. 117.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF₁.alpha.,a compound according to claim
 1. 118.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 119.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 120.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 121.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF₁α,a compound according to claim
 1. 122.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 123.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 124.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 125.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 126.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 127.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 128.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 129.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 130.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 131.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 132.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF₁α,a compound according to claim
 1. 133.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 134.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 135.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 136.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 137.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 138.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim
 1. 139.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF₁α,a compound according to claim
 1. 140.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α,a compound according to claim
 1. 141.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-(m-chlorphenoxy)-17,18,19,20-tetranor-cis-13-PGF₁.alpha.,a compound according to claim
 1. 142.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF₁α,a compound according to claim
 1. 143.2-Decarboxy-2-aminomethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF₁α,a compound according to claim 1.